


Plunder

by thegrendel



Category: Original Work
Genre: Anal Sex, Dildos, F/M, Gigolo, Older Woman/Younger Man, Pegging, Redemption, Regret, Sex Club, Unintended Consequences, male escorts, male prostitute
Language: English
Status: Completed
Published: 2018-08-08
Updated: 2018-08-08
Packaged: 2019-06-23 20:40:45
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,788
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15614562
Author URL: https://archiveofourown.org/users/thegrendel/pseuds/thegrendel
Summary: The Club had a very special clientele: women who were willing to pay $500 per hour for sex with male escorts. Even kinky sex. Even very kinky sex. But sometimes a client would fall in love with her escort ...





	Plunder

Her eyes tracked the server's tight little butt as he strode away with the  
order. That was one of the attractions of this place, the handsome young  
studs who waited tables . . . and their unusual uniforms. Domino masks  
covered their eyes (conjuring up thoughts of _The Lone Ranger_ ).  
They wore formal tuxedos, complete with cummerbund and top hat, but  
the pants were form-fitting -- very much so -- and the entire seat was  
cut away to expose the buttocks. Naked, finely-muscled buttocks. A very  
suggestive rear view.

Eileen had a sudden desire to summon him back and ask him upstairs.  
But no, the evening was still young and there were so many others to  
choose from. The rooms at the top of the stairs cost $500 per hour, not  
counting a tip for the chosen escort. But, _damn_ , he had buns to  
die for. Maybe later . . .

Half an hour later they were upstairs in the small room. Jason was  
lying on the narrow bed, facedown. He still wore his mask, but nothing  
else. From the crack of his hind cheeks there protruded a slim rubber  
hose leading to an old-fashioned red rubber enema bag suspended from a  
rusty coat hook. Eileen needed him immaculate both outside and in for  
what she had in mind. Even the simple act of inserting the nozzle into  
him had left her flushed and excited.

Girl, this better be worth it, she thought as she buckled on her harness,  
then secured the oversize gleaming chrome-plated dildo in the retaining  
ring. This little evening outing at the Plunder Club was going to  
plunder her savings for more than she could afford. Quite a bit more.
    
    
        I deserve life's little pleasures. Damned if I don't! Haven't I had
        to fight for everything as long as I can remember?
    
        I was the first one in the family ever to attend college. Years of
        grunt work as a typist, receptionist, secretary, and general office
        slave. Got my first real break when the VP of production chose me
        as his assistant. I'm finally pulling down a halfway decent wage,
        but at what cost? Working long hours, going to night school to get
        my grad degree, giving up any pretense of a social life.
    
        Relationships? No time. Romance? That exists only in pulp novels and
        the movies. Sex? Empty-headed idiots clumsily pawing my body. Now
        it's my turn. This one's for me..
    

The gurgle of the commode in the adjoining bathroom signaled that  
Jason had finished flushing away the enema solution and various other  
contents of his bowels. Good -- nice and neat. Squeaky clean right  
where it counted. Eileen was very much into strapons and anal sex, but  
she just hated the little surprises -- the messes and the stenches --  
that all too often accompanied it.
    
    
      She remembered the first time. Her initiation into anal.
      It was the summer after graduation, and she had just turned 18.
      She was working as a camp counselor. On a dare from one of her
      friends, she had impulsively jumped into a shower stall with
      the director. He was hung like a horse, according to rumor.
     "He'll screw anything on two legs," they said. Eileen had to
      have him.
    
      He just laughed, and took her arm. She let him turn her around
      and bend her over. "Reach back and spread your cheeks," he said.
      What? "Spread 'em, little girl. I can get pussy any time.
      It's your ass I want."
    
      This wasn't quite what she had in mind, but . . . she had
      fantasized about that sort of thing. Those of her girlfriends
      who had tried it either found it disgustingly dirty or raved
      about how utterly fantastic it was.
    
     "Come on, baby. I know what I'm doing. You'll enjoy it as much
      as I will, maybe even more. I'm not gonna force you, but make
      up your mind. Either open up your ass for me or get the hell
      out of here."
    
      She had to choose. Now. She hesitated, then bent over.
    
      It stung a little going in. He had "lubed" himself up with soap,
      and it felt like a rather large cucumber sliding in and out of
      her. In and out of her rear passage. It was actually starting to
      arouse her by the time he came. He scrubbed her back and helped
      towel her dry. Very considerate.
    
      Later, she had a bout of diarrhea. The soap must have irritated her
      gut. And yet the memory of it haunted her. . . .
    

His eyes widened momentarily as he entered the room. She already had  
on her equipment belt and her tool was ready and waiting. Most clients  
liked kisses, caresses, and a little foreplay before the going got hot  
and heavy. This woman obviously didn't need any preliminaries.

She pointed at the bed. _Bend over_ , her abrupt hand motion  
indicated. Talking wasn't part of the protocol here, and it just got in  
the way of the action anyhow.

He had already lubed himself as part of the bathroom routine, but she  
wanted to make doubly sure. Or maybe she just needed an excuse to grope  
around inside his butthole. No matter. This was included in the basic  
services the clients paid for. He bent over the bed.

She liked it hard and brutal. Her grunts punctuated the silence as she  
slammed in and out of him. Small, involuntary farts escaped from her,  
unnoticed in her excitement. Trained to fully relax his sphincter ring  
muscles, he still felt the stretch and friction as she plowed his ass  
(damn, that was some heavy metal she had on). Despite his professional  
detachment, it was turning him on. He felt his dick slowly hardening  
beneath him.

She screamed in triumph as she collapsed atop his muscular back. (The  
rooms were more or less soundproof.) The sweat from her bare breasts  
mingled with his own. She held on tight to his hips for a moment more,  
then withdrew out of him with a sound like a vacuum seal being popped. He  
rolled over, and she giggled as she saw his erection. She grasped it  
hard in her fist and pulled it toward her.

An open-palm gesture informed her that this was an extra-cost service.  
She shrugged and pulled two fifties out of the leather pocketbook on  
the nightstand. A slight shake of the head from him and she fished out  
another fifty. That got her a nod and a smile. It was _her_ turn  
to bend over.

He touched her pussy. It was sopping wet. She raised her right fist and  
pumped it. Into her then, doggy style. His training included delaying  
ejaculation, and twenty minutes later he was still hard inside her. A  
synchronized clit massage had brought her three orgasms, but she craved  
something more. Craved it badly.

She slapped his flank twice, indicating he should pull out. He complied.  
Reaching behind herself, she inserted an index finger into the crack  
between her buttocks. No mistaking _that_ message. He held up three  
fingers. That would cost another three hundred (ouch!). She ransacked  
the pocketbook and somehow managed to scrape it together. Beans and  
canned spaghetti for the rest of the month, but fuck that. (No, fuck  
me! Now! In the ass, you beautiful stud.)

Eileen smiled as she drifted off to sleep in her own bed later that  
night. She had a pleasant ache in her loins . . . and elsewhere. Over  
a thousand dollars poorer but with memories no one could ever take away  
from her -- memories of bare flesh and white-hot explosive sex.

 

Six months later she was back at the club. Her finances were once more  
healthy enough to plunder, and she wanted to plunder Jason again.  
She _needed_ him. He had haunted her dreams and intruded into  
her daytime thoughts.

The evening dragged on, and still no Jason. Masked as the servers were,  
she would have recognized his bare behind in an instant. There was a  
feast of deliciously naked male buttocks out there, but none belonging  
to _him_. Where was he?

A hundred-dollar bill bought her the information that Jason had left  
for parts unknown several months back. She staggered out of the club,  
tearing at her hair, sobbing. Gone! The object of her desires -- lost.

 

"Jensen 'Jason' Warnecke," the private detective was saying. "We've  
managed to track him as far as the Port Authority Terminal in New York  
City. Further than that . . ." He shrugged his shoulders.

Jason, it turned out, was quite a character. A _shady_ character.  
He had an extensive police record -- fraud, embezzlement, and once,  
selling drugs. Twenty years old and a hardened criminal already.  
No matter. Eileen had to find him. _Had_ to. Every cell in her  
body cried out for him.

"Yes, ma'am. We've got a warrant out for him. If you see someone  
matching his description, call us." The desk sergeant at the 91st  
Precinct hadn't been very helpful. At least now she knew that someone  
who looked like him had been seen near a crack house on 5th Street,  
off Avenue D. Drugs. No. Please, no.

"Yeah, lady, maybe I seen da guy, maybe not. What's it worth to ya?" The  
boy had steely, world-wise eyes. The bidding went up to twenty before  
the street urchin motioned her to follow and ran off.

He lay on a dirty mattress in a dark room. There was an overpowering  
stench of decay and human waste.

"Jason, Jason, what's _happened_ to you?" 

"Drug OD, lady," the boy said. "Prolly he'll croak any time now."

She had his head cradled on her lap and her teardrops streaked the dirt on  
his face. His eyes opened.

"I dunno -- yeah, maybe I remember you." He grimaced. "The dame who  
couldn't get enough. Wild, wild woman. Did me, then I did her, then . . ."

"Jason, I think . . . I think I love you. Hang on. I'll get help. I'll  
make you well again."

"Too late, lady," the boy said. Jason had gone limp in her arms.

 

All this had happened some years back. Before people wised up. Before  
most everyone became paranoid about anonymous sex. Before AIDS.

The authorities closed down the Plunder Club. Later it reopened, under  
new management, and considerably tamed down. The servers no longer had  
bare parts of their anatomy on display, and the upstairs rooms were off  
limits to the clientele. The food and drink had improved, though.

Eileen has done quite well for herself in the meantime. I should know.  
We're partners in Entertainment Holdings, Inc. It's the biggest outfit  
of its kind in the region, and one of our hottest properties is the new  
Plunder Club. I'm also her lover and confidante.

Twice a week we both do volunteer work at the local drug hotline. We've  
saved quite a few people from Jason's fate.


End file.
